Identification of amino acid substitutions that confer a high affinity for sulfaphenazole binding and a high catalytic efficiency for warfarin metabolism to P450 2C19

Biochemistry

Volumn 37, Issue 46, 1998, Pages 16270-16279

  Jung, Frank ^a,b   Griffin, Keith J ^a   Song, Wu ^a,c   Richardson, Toby H ^a,d   Yang, Mierha ^a   Johnson, Eric F ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b FRESENIUS MEDICAL CARE   (Germany)

^c Applied Biotech Inc   (United States)

^d DIVERSA CORPORATION   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHIMERIC PROTEIN; CYTOCHROME P450; CYTOCHROME P450 2C19; CYTOCHROME P450 2C9; PHENYTOIN; SULFAPHENAZOLE; TOLBUTAMIDE; UNCLASSIFIED DRUG; WARFARIN;

AMINO ACID SUBSTITUTION; ARTICLE; DRUG METABOLISM; ENZYME PURIFICATION; ESCHERICHIA COLI; NUCLEOTIDE SEQUENCE; PRIORITY JOURNAL; PROTEIN STABILITY; SITE DIRECTED MUTAGENESIS; STEREOSPECIFICITY;

AMINO ACID SEQUENCE; AMINO ACID SUBSTITUTION; ARYL HYDROCARBON HYDROXYLASES; BINDING, COMPETITIVE; CATALYSIS; CELL MEMBRANE; CYTOCHROME P-450 ENZYME SYSTEM; ENZYME INHIBITORS; ESCHERICHIA COLI; GENETIC VECTORS; HUMANS; MIXED FUNCTION OXYGENASES; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; MUTAGENESIS, SITE-DIRECTED; RECOMBINANT FUSION PROTEINS; STEREOISOMERISM; SULFAPHENAZOLE; WARFARIN;

EID: 0032542015     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi981704c     Document Type: Article

References (46)

1. Romkes, M., Faletto, M. B., Blaisdell, J. A., Raucy, J. L., and Goldstein, J. A. (1991) Biochemistry 30, 3247-3255.
2. Richardson, T. H., Jung, F., Griffin, K. J., Wester, M., Raucy, J. L., Kemper, B., Bornheim, L. M., Hassett, C., Omiecinski, C. J., and Johnson, E. F. (1995) Arch. Biochem. Biophys. 323, 87-96.
3. Goldstein, J. A., Ishizaki, T., Chiba, K., de Morais, S. M., Bell, D., Krahn, P. M., and Evans, D. A. (1997) Pharmacogenetics 7, 59-64.
4. Jung, F., Richardson, T. H., Raucy, J. L., and Johnson, E. F. (1997) Drug Metab. Dispos. 25, 133-139.
5. Bajpai, M., Roskos, L. K., Shen, D. D., and Levy, R. H. (1996) Drug Metab. Dispos. 24, 1401-1403.
6. Kaminsky, L. S., De Morais, S. M. F., Faletto, M. B., Dunbar, D. A., and Goldstein, J. A. (1993) Mol. Pharmacol. 43, 234-239.
7. Rettie, A. E., Korzekwa, K. R., Kunze, K. L., Lawrence, R. F., Eddy, A. C., Aoyama, T., Gelboin, H. V., Gonzalez, F. J., and Trager, W. F. (1992) Chem. Res. Toxicol. 5, 54-59.
8. De Morais, S. M. F., Wilkinson, G. R., Blaisdell, J., Nakamura, K., Meyer, U. A., and Goldstein, J. A. (1994) J. Biol. Chem. 269, 15419-15422.
9. Goldstein, J. A., Faletto, M. B., Romkes-Sparks, M., Sullivan, T., Kitareewan, S., Raucy, J. L., Lasker, J. M., and Ghanayem, B. I. (1994) Biochemistry 33, 1743-1752.
10. Karam, W. G., Goldstein, J. A., Lasker, J. M., and Ghanayem, B. I. (1996) Drug Metab. Dispos. 24, 1081-1087.
11. Ibeanu, G. C., Ghanayem, B. I., Linko, P., Li, L. P., Pedersen, L. G., and Goldstein, J. A. (1996) J. Biol. Chem. 271, 12496-12501.
12. Miners, J. O., Smith, K. J., Robson, R. A., McManus, M. E., Veronese, M., and Birkett, D. J. (1988) Biochem. Pharmacol. 37, 1137-1144.
13. Veronese, M. E., McManus, M. E., Laupattarakasem, P., Miners, J. O., and Birkett, D. J. (1990) Drug Metab. Dispos. 18, 356-361.
14. Baldwin, S. J., Bloomer, J. C., Smith, G. J., Ayrton, A. D., Clarke, S. E., and Chenery, R. J. (1995) Xenobiotica 25, 261-270.
15. Veronese, M. E., Mackenzie, P. I., Doecke, C. J., McManus, M. E., Miners, J. O., and Birkett, D. J. (1991) Biochem. Biophys. Res. Commun. 175, 1112-1118.
16. Mancy, A., Dijols, S., Poli, S., Guengerich, F. P., and Mansuy, D. (1996) Biochemistry 35, 16205-16212.
17. Steward, D. J., Haining, R. L., Henne, K. R., Davis, G., Rushmore, T. H., Trager, W. F., and Rettie, A. E. (1997) Pharmacogenetics 7, 361-367.
18. Estabrook, R. W., and Werringloer, J. (1978) Methods Enzymol. 52, 212-220.
19. Fasco, M. J., Piper, L. J., and Kaminsky, L. S. (1977) J. Chromatogr. 131, 365-373.
20. Yasukochi, Y., and Masters, B. S. S. (1976) J. Biol. Chem. 251, 5337-5344.
21. Johnson, E. F., Schwab, G. E., and Muller-Eberhard, U. (1979) Mol. Pharmacol. 15, 708-717.
22. Omura, T., and Sato, R. (1964) J. Biol. Chem. 239, 2379-2385.
23. Sali, A., and Blundell, T. L. (1993) J. Mol. Biol. 234, 779-815.
24. Li, H. Y., and Poulos, T. L. (1997) Nat. Struct. Biol. 4, 140-146.
25. Mansuy, D., Battioni, P., Chottard, J. C., Riche, C., and Chiaroni, A. (1983) J. Am. Chem. Soc. 105, 455-463.
26. Poli-Scaife, S., Attias, R., Dansette, P. M., and Mansuy, D. (1997) Biochemistry 36, 12672-12682.
27. Harlow, G. R., He, Y. A., and Halpert, J. R. (1997) Biochim. Biophys. Acta 1338, 259-266.
28. Von Wachenfeldt, C., and Johnson, E. F. (1995) in Cytochrome P450: Structure, Mechanism, and Biochemistry (Second Edition) (Ortiz de Montellano, P. R., Ed.) pp 183-244, Plenum Press, New York.
29. Gotoh, O. (1992) J. Biol. Chem. 267, 83-90.
30. Hasemann, C. A., Kurumbail, R. G., Boddupalli, S. S., Peterson, J. A., and Deisenhofer, J. (1995) Structure 3, 41-62.
31. Ravichandran, K. G., Boddupalli, S. S., Hasemann, C. A., Peterson, J. A., and Deisenhofer, J. (1993) Science 261, 731-736.
32. Paulsen, M. D., and Ornstein, R. L. (1995) Proteins 21, 237-243.
33. Modi, S., Paine, M. J., Sutcliffe, M. J., Lian, L. Y., Primrose, W. U., Wolf, C. R., and Roberts, G. C. K. (1996) Biochemistry 35, 4540-4550.
34. De Groot, M. J., Vermeulen, N. P. E., Kramer, J. D., Van Acker, F. A. A., and Den Kelder, G. M. D. O. (1996) Chem. Res. Toxicol. 9, 1079-1091.
35. Szklarz, G. D., He, Y. A., and Halpert, J. R. (1995) Biochemistry 34, 14312-14322.
36. Chang, Y. T., Stiffelman, O. B., Vakser, I. A., Loew, G. H., Bridges, A., and Waskell, L. (1997) Protein Eng. 10, 119-129.
37. Jones, B. C., Hawksworth, G., Horne, V. A., Newlands, A., Morsman, J., Tute, M. S., and Smith, D. A. (1996) Drug Metab. Dispos. 24, 260-266.
38. Jones, J. P., He, M. X., Trager, W. F., and Rettie, A. E. (1996) Drug Metab. Dispos. 24, 1-6.
39. Mancy, A., Broto, P., Dijols, S., Dansette, P. M., and Mansuy, D. (1995) Biochemistry 34, 10365-10375.
40. Wolff, T., Distlerath, L. M., Worthington, M. T., Groopman, J. D., Hammons, G. J., Kadlubar, F. F., Prough, R. A., Martin, M. V., and Guengerich, F. P. (1985) Cancer Res. 45, 2116-2122.
41. Meyer, U. A., Gut, J., Kronbach, T., Skoda, C., Meier, U. T., Catin, T., and Dayer, P. (1986) Xenobiotica 16, 449-464.
42. Islam, S. A., Wolf, C. R., Lennard, M. S., and Sternberg, M. J. E. (1991) Carcinogenesis 12, 2211-2219.
43. Koymans, L., Vermeulen, N. P. E., van Acker, S. A. B. E., te Koppele, J. M., Heykants, J. J. P., Lavrijsen, K., Meuldermans, W., and den Kelder, G. M. D. (1992) Chem. Res. Toxicol. 5, 211-219.
44. Mackman, R., Tschirret-Guth, R. A., Smith, G., Hayhurst, G. P., Ellis, S. W., Lennard, R. S., Tucker, G. T., Wolf, C. R., and Ortiz De Montellano, P. R. (1996) Arch. Biochem. Biophys. 331, 134-140.
45. Cleland, W. W., and Kreevoy, M. M. (1994) Science 264, 1887-1890.
46. Kraulis, P. J. (1991) J. Appl. Crystallogr. 24, 946-950.